AR107099A1 - ESPIRO- [HETEROCICLOALCANE INDOLIN] COMPOUNDS AS PHOSPHODESTERASE INHIBITORS - Google Patents

ESPIRO- [HETEROCICLOALCANE INDOLIN] COMPOUNDS AS PHOSPHODESTERASE INHIBITORS

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Publication number
AR107099A1
AR107099A1 ARP160103951A ARP160103951A AR107099A1 AR 107099 A1 AR107099 A1 AR 107099A1 AR P160103951 A ARP160103951 A AR P160103951A AR P160103951 A ARP160103951 A AR P160103951A AR 107099 A1 AR107099 A1 AR 107099A1
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AR
Argentina
Prior art keywords
alkyl
alkylene
nhs
mono
membered heterocycloalkyl
Prior art date
Application number
ARP160103951A
Other languages
Spanish (es)
Inventor
Dr Hesslinger Christian
Welbers Andr
Dr Wagener Markus
Dr Jakob Florian
Dr Konetzki Ingo
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Gruenenthal Gmbh
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Application filed by Gruenenthal Gmbh filed Critical Gruenenthal Gmbh
Publication of AR107099A1 publication Critical patent/AR107099A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/10—Spiro-condensed systems
    • C07D491/107—Spiro-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Rheumatology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Reivindicación 1: Un compuesto de la fórmula (1) caracterizado porque A, B y C representan en forma independiente CH o N; m es 0, 1, 2 ó 3 y n es 0, 1, 2 o 3, con la salvedad de que la suma de (m + n) sea 2, 3 ó 4; L se selecciona del grupo que consiste en C(=O)NR², S(=O), S(=O)₂, S(=O)₂NR², P(=O)(R²), O ó una unión; R¹ se selecciona de C₁₋₆-alquilo, no sustituido o mono- o polisustituido; o cicloalquilo C₃₋₆ o heterocicloalquilo de 3 a 7 miembros, en cada caso instituido o mono o polisustituido; R² se selecciona de H o alquilo C₁₋₆, no sustituido o mono- o polisustituido; o R¹ y R² junto con el átomo de nitrógeno al cual están unidos forman un heterocicloalquilo de 3 a 12 miembros, donde dicho heterocicloalquilo de 3 a 12 miembros puede contener uno o dos heteroátomos adicionales seleccionados del grupo que consiste en O, S y N y pueden ser mono- o bicíclicos y donde dicho heterocicloalquilo de 3 a 12 miembros está instituido o es mono o polisustituido; G representa un fenilo o heteroarilo de 5 a 6 miembros donde dicho fenilo o dicho heteroarilo de 5 a 6 miembros no está sustituido con uno, dos, tres o cuatro sustituyentes Z; donde Z en cada ocurrencia se selecciona del grupo que consiste en halógeno, OH, CN, SH, NO₂, C₁₋₆-alquilo, C₂₋₆-alquenilo, C₂₋₆ alquinilo, C₁₋₆-hidroxialquilo, C₁₋₆-cianoalquilo, C₁₋₆-alcoxi, C₁₋₆-tioalquilo, C₁₋₆-haloalquilo, (C₁₋₆-alcoxi)-(C₁₋₆alquilenilo), (C₁₋₆-alcoxi)-C₁₋₆-alcoxi, C₁₋₆-tiohaloalquilo, C₁₋₆-haloalcoxi, (C₁₋₆-tioalquil)-(C₁₋₆-alquenilo), C₃₋₆-cicloalquilo, (C₃₋₆-cicloalquil)-(C₁₋₃-alquilenilo), heterocicloalquilo de 3 a 7 miembros, (heterocicloalquilo de 3 a 7 miembros)-(C₁₋₃-alquilenilo), dicho C₃₋₆-cicloalquil y dicho heterocicloalquilo de 3 a 7 miembros en cada caso no están sustituidos o están mono o poli sustituidos NH₂, NH(C₁₋₆-alquilo), N(C₁₋₆-alquil)₂, NHCO(C₁₋₆-alquilo), NHCO₂(C₁₋₆-alquilo), NHC(O)NH₂, NHCONH(C₁₋₆-alquilo), NHCON(C₁₋₆-alquil)₂, (C₁₋₆-alquileno)NH₂, (C₁₋₆-alquileno)NH(C₁₋₆-alquilo), (C₁₋₆-alquileno)N(C₁₋₆-alquil)₂, (C₁₋₆-alquileno)NHCO(C₁₋₆-alquilo), (C₁₋₆-alquileno)NHCO₂(C₁₋₆-alquilo), (C₁₋₆-alquileno)NHC(O)NH₂, (C₁₋₆-alquileno) NHCONH(C₁₋₆-alquilo), (C₁₋₆-alquileno)NHCON(C₁₋₆-alquil)₂, NH(C₁₋₆-alquileno)-CO₂(C₁₋₆-alquilo), NH(C₁₋₆-alquileno)-CONH₂, NH(C₁₋₆-alquileno)-CONH(C₁₋₆-alquilo), NH(C₁₋₆-alquileno)-CON(C₁₋₆-alquil)₂, NHS(O)₂OH, NHS(O)₂(C₁₋₆-alquilo), NHS(O)₂(C₁₋₆-alquilo), NHS(O)₂NH₂, NHS(O)₂NH(C₁₋₆-alquilo), NHS(O)₂N(C₁₋₆-alquil)₂, NH(C₁₋₆-alquileno)-S(O)₂OH, NH(C₁₋₆-alquileno)-S(O)₂(C₁₋₆-alquilo), NH(C₁₋₆-alquileno)-S(O)₂O(C₁₋₆-alquilo), NH(C₁₋₆-alquileno)-S(O)₂NH₂, NH(C₁₋₆-alquileno)-S(O)₂NH(C₁₋₆alquilo), CO₂H, CO(C₁₋₆-alquilo), CO₂(C₁₋₆-alquilo), O-CO(C₁₋₆-alquilo), O-CO₂(C₁₋₆-alquilo), CONH₂, CONH(C₁₋₆-alquilo), CON(C₁₋₆-alquil)₂, OCONH(C₁₋₆-alquilo), OCON(C₁₋₆-alquil)₂, OS(O)₂(C₁₋₆-alquilo), OS(O)₂OH, OS(O)₂O(C₁₋₆-alquilo), OS(O)₂NH₂, OS(O)₂NH(C₁₋₆-alquilo), OS(O)₂N(C₁₋₆-alquil)₂, S(O)(C₁₋₆-alquilo), S(O)₂(C₁₋₆-alquilo), S(O)₂OH, S(O)₂O(C₁₋₆-alquilo), S(O)₂NH₂, S(O)₂NH(C₁₋₆-alquilo), y S(O)₂N(C₁₋₆-alquil)₂; opcionalmente en la forma de un estereoisómero individual o una mezcla de estereoisómeros, en la forma del compuesto libre y/o una sal fisiológicamente aceptable y/o un solvato fisiológicamente aceptable de las anteriores.Claim 1: A compound of the formula (1) characterized in that A, B and C independently represent CH or N; m is 0, 1, 2 or 3 and n is 0, 1, 2 or 3, with the proviso that the sum of (m + n) is 2, 3 or 4; L is selected from the group consisting of C (= O) NR², S (= O), S (= O) ₂, S (= O) ₂NR², P (= O) (R²), O or a union; R¹ is selected from C₁₋₆-alkyl, unsubstituted or mono- or polysubstituted; or C₃₋₆ cycloalkyl or 3 to 7 membered heterocycloalkyl, in each case instituted or mono or polysubstituted; R² is selected from H or C₁₋₆ alkyl, unsubstituted or mono- or polysubstituted; or R¹ and R² together with the nitrogen atom to which they are attached form a 3-12 membered heterocycloalkyl, wherein said 3 to 12 membered heterocycloalkyl may contain one or two additional heteroatoms selected from the group consisting of O, S and N and they can be mono- or bicyclic and where said 3 to 12-membered heterocycloalkyl is instituted or is mono or polysubstituted; G represents a 5 to 6 membered phenyl or heteroaryl wherein said phenyl or said 5 to 6 membered heteroaryl is not substituted with one, two, three or four Z substituents; where Z in each occurrence is selected from the group consisting of halogen, OH, CN, SH, NO₂, C₁₋₆-alkyl, C₂₋₆-alkenyl, C₂₋₆ alkynyl, C₁₋₆-hydroxyalkyl, C₁₋₆-cyanoalkyl , C₁₋₆-alkoxy, C₁₋₆-thioalkyl, C₁₋₆-haloalkyl, (C₁₋₆-alkoxy) - (C₁₋₆alkylene), (C₁₋₆-alkoxy) -C₁₋₆-alkoxy, C₁₋₆ -thiohaloalkyl, C₁₋₆-haloalkoxy, (C₁₋₆-thioalkyl) - (C₁₋₆-alkenyl), C₃₋₆-cycloalkyl, (C₃₋₆-cycloalkyl) - (C₁₋₃-alkylenyl), heterocycloalkyl of 3 to 7 members, (3 to 7-membered heterocycloalkyl) - (C₁₋₃-alkylenyl), said C₃₋₆-cycloalkyl and said 3 to 7 membered heterocycloalkyl in each case are not substituted or are mono or poly substituted NH₂, NH (C₁₋₆-alkyl), N (C₁₋₆-alkyl) ₂, NHCO (C₁₋₆-alkyl), NHCO₂ (C₁₋₆-alkyl), NHC (O) NH₂, NHCONH (C₁₋₆-alkyl) , NHCON (C₁₋₆-alkyl) ₂, (C₁₋₆-alkylene) NH₂, (C₁₋ -alkylene) NH (C₁₋₆-alkyl), (C₁₋₆-alkylene) N (C₁₋₆-alkyl) ₂, (C₁₋₆-alkylene) NHCO (C₁₋₆-alkyl), (C₁₋₆- alkylene) NHCO₂ (C₁₋₆-alkyl), (C₁₋₆-alkylene) NHC (O) NH₂, (C₁₋₆-alkylene) NHCONH (C₁₋₆-alkyl), (C₁₋₆-alkylene) NHCON (C₁ ₋₆-alkyl) ₂, NH (C₁₋₆-alkylene) -CO₂ (C₁₋₆-alkyl), NH (C₁₋₆-alkylene) -CONH₂, NH (C₁₋₆-alkylene) -CONH (C₁₋₆ -alkyl), NH (C₁₋₆-alkylene) -CON (C₁₋₆-alkyl) ₂, NHS (O) ₂OH, NHS (O) ₂ (C₁₋₆-alkyl), NHS (O) ₂ (C₁₋ ₆-alkyl), NHS (O) ₂NH₂, NHS (O) ₂NH (C₁₋₆-alkyl), NHS (O) ₂N (C₁₋₆-alkyl) ₂, NH (C₁₋₆-alkylene) -S (O ) ₂OH, NH (C₁₋₆-alkylene) -S (O) ₂ (C₁₋₆-alkyl), NH (C₁₋₆-alkylene) -S (O) ₂O (C₁₋₆-alkyl), NH (C₁ ₋₆-alkylene) -S (O) ₂NH₂, NH (C₁₋₆-alkylene) -S (O) ₂NH (C₁₋₆alkyl), CO₂H, CO (C₁₋₆-alkyl), CO₂ (C₁₋₆-alkyl ), O-CO (C₁₋₆-alkyl), O-CO₂ (C ₁₋₆-alkyl), CONH₂, CONH (C₁₋₆-alkyl), CON (C₁₋₆-alkyl) ₂, OCONH (C₁₋₆-alkyl), OCON (C₁₋₆-alkyl) ₂, OS (O ) ₂ (C₁₋₆-alkyl), OS (O) ₂OH, OS (O) ₂O (C₁₋₆-alkyl), OS (O) ₂NH₂, OS (O) ₂NH (C₁₋₆-alkyl), OS ( O) ₂N (C₁₋₆-alkyl) ₂, S (O) (C₁₋₆-alkyl), S (O) ₂ (C₁₋₆-alkyl), S (O) ₂OH, S (O) ₂O (C₁ ₋₆-alkyl), S (O) ₂NH₂, S (O) ₂NH (C₁₋₆-alkyl), and S (O) ₂N (C₁₋₆-alkyl) ₂; optionally in the form of an individual stereoisomer or a mixture of stereoisomers, in the form of the free compound and / or a physiologically acceptable salt and / or a physiologically acceptable solvate of the foregoing.

ARP160103951A 2015-12-22 2016-12-21 ESPIRO- [HETEROCICLOALCANE INDOLIN] COMPOUNDS AS PHOSPHODESTERASE INHIBITORS AR107099A1 (en)

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CN114031558A (en) * 2021-12-14 2022-02-11 无锡捷化医药科技有限公司 Preparation method of 1- (6-chloropyridazin-4-yl) ethyl-1-ketone

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WO2014128585A1 (en) * 2013-02-19 2014-08-28 Pfizer Inc. Azabenzimidazole compounds as inhibitors of pde4 isozymes for the treatment of cns and other disorders
TW201512189A (en) * 2013-04-16 2015-04-01 Gruenenthal Chemie Novel substituted condensed pyrimidine compounds
AR101196A1 (en) * 2014-07-16 2016-11-30 Gruenenthal Gmbh SUBSTITUTED PYRIMIDINE COMPOUNDS

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